Animal growth promoters

ABSTRACT

AN ANIMAL FEED, ESPECIALLY FOR MEAT-PRODUCING ANIMALS SUCH AS SWINE, RUMINANTS, POULTRY, ETC., WHICH CONTAINS AN AMOUNT OF 3-(P-LOWERALKOXYPHENYL) OR 3-(P-HYDROXYPHENYL) OR 3-(P-BENZYLOXYPHENYL)-4-N-PROPYL-7-HYDROXYCOUMARIN EFFECTIVE TO PROMOTE THE RATE OF GROWTH, E.G., WEIGHT GAIN, AND FEED CONVERSION OF THE ANIMAL BEING FED.

United States Patent 3,663,705 ANIMAL GROWTH PROMOTERS Richard N. Hui-d, Terre Haute, Ind., assignor to Commercial Solvents Corporation, New York, N.Y. N0 Drawing. Filed Apr. 6, 1970, Ser. No. 26,123

Int. Cl. A61k 27/00 U.S. Cl. 424-281 Claims ABSTRACT OF THE DISCLOSURE An animal feed, especially for meat-producing animals such as swine, ruminants, poultry, etc., which contains an amount of 3-(p-loweralkoxyphenyl) or 3-(p-hydroxyphenyl) or S-(p-benzyloxyphenyl)-4-n-propyl-7-hydroxycoumarin effective to promote the rate of growth, e.g., weight gain, and feed conversion of the animal being fed.

This invention relates to feed supplements for animals and their administration, and more particularly to novel animal feeds including feed compositions for swine, ruminants, e.g., cattle, sheep, and lamb, and poultry, which compositions contain an amount of 3-(p-loweralkoxyphenyl) or S-(hydroxyphenyl) or 3-(p benzyloxyphenyl)-'4-n-propyl-7-hydroxycoumarin effective to promote the rate of growth of the animal being fed.

' According to the present invention, a small amount of 3-(p-loweralkoxyphenyl) or 3-(p-hydroxyphenyl) or 3- (p-benzyloxyphenyl)-4-n-propyl 7 hydroxycoumarin, see general formula below, is added to animal feed rations such as lamb and poultry rations to provide improved animal growth, e.g. rate of weight gain, and better feed efiiciency. The inclusion in conventional animal diets and feeds, e.g. meat-producing animal feeds such as ruminant feeds, swine feeds and poultry feeds has a particularly stimulating elfect on growth and rate of weight gain. The coumarins are particularly employed with altered males and female animals, especially the latter. The coumarins employed in the compositions of this invention have the structural formula:

wherein R is hydrogen, lower alkyl or benzyLWhen R is --CH the compound is designated Formula 1 and is also known as 3 (p methoxyphenyl)-4-n-propyl-7-hydroxycoumarin.

The coumarins can be administered to animals by any suitable method including. oral and parenteral administrations. For example, they can be blended with ordinary feed containing nutritional values in an amount suflicient to produce the desired rate of growth and can thus be fed directly to the animals, or the compound can be suspended in a suitable injection suspension medium such as peanut oil and injected parenterally. The amount of coumarin fed to an animal, of course, varies depending upon the animal, desired rate of growth and the like.

When the coumarin is to be administered in feeds, an animal feed composition can be prepared containing the usual nutritionally-balanced quantities of carbohydrates, proteins, vitamins and minerals, together with the compound of the present invention. Some of these usual dietary elements are grains, such as ground grain and grain byproducts; animal protein substances, such as those found in fish meal and meat scraps, vegetable proteins like soybean oil meal or peanut oil meal; vitaminaceous materials, e.g., vitamin A and D mixtures; riboflavin supplements and other vitamin B complex members; and bone meal and limestone to provide minerals.

The coumarin compounds employed in this invention can be mixed with the feed by any conventional means. This can be done advantageously by grinding such a compound with some of the grain, such as, for instance, corn, or with other components of conventional animal feed such as vitamins, soybean meal, choline chloride, limestone flour, granite flour, oyster shell flour, fish flour, or the like, to provide a concentrated feed supplement composition containing the compound in any convenient amount. Generally, the concentrate will contain from about one percent, or more, e.g. about 5 to 50% by weight of the compound. The ground mixture can then be further mixed in a proper proportion with the feed.

It will be understood that the feed supplement in the nature of a concentrate consisting of such a compound and a solid or liquid carrier can be sold to the trade for incorporation in feeds. When so used, the compound will be present in the feed supplement concentrate in suflicient quantity to give the desired ratio of the compound to feed in the final composition fed to animals. The carrier present in the feed supplements of this invention may or may not have nutritional value. As illustrative of the solid carriers which can be employed in the novel feed supplements, there can be named soybean meal, choline chloride, vitamins (i.e. riboflavin, niacin, vitamin B vitamin D), cottonseed meal, corn, mineral mixtures, walnut shells, diatomaceous earth, and the like. Illustrative of liquid carriers are water, molasses, vegetable oils, animal fats, nontoxic solutions containing urea, phosphates and other nutrients. These named carriers along with any others known in the feed industry to be employed in feed supplements can be used in the compositions of this invention.

The amount of the coumarin compound added to the animal diet and the period of administration will depend upon the attendant circumstances and the nature of the effect desired as well as the animal to be treated. The level of the compound in the feed generally should not be less than about 0.0001%, preferably about O.0OO5%, nor greater than about 0:02, preferably about 0.01%, based on the weight of the animals feed. The compound will normally be administered to the animal during the period in which it is being raised to increase its weight to that desired. For example, with chickens the period of administration will vary depending upon whether broilers or fryers as desired. The period will range from day-old chicks to chickens of the desired weight, this being for broilers about two and a half to three pounds dressed, rather than to a specific age, but normally the chickens are about 9 to 12, or 16, or more, weeks in age. For larger meat producing animals such as lambs, cattle and swine, the compound can be used with the initial baby animal feeds and throughout the growing and weight gain pe riod of the animal, e.g. until slaughter. The period of administration can vary with such larger animals from a few months, i.e., 1 to 6 months up to several years, i.e., 1 to 3 years, depending upon the desired age and weight of the animal. Expressed in another way, the amount of active compound within the scope of this invention provided in the animals feed will ordinarily be within the range from about 1 to 150 grams, preferably about 4 or 5 to 100 grams, of the compound per ton of animal feed over the desired period of administration. A particular amount for chickens is about 25 to 100 grams per ton of feed.

In order that the invention may be better understood, the following illustrative examples are given. Those skilled in the art will appreciate that other compositions according to this invention can be prepared and applied in accordance with the examples.

EXAMPLE I Day-old Cornish Cross broiler chicks are allocated to five replicates of ten birds each sex and fed basal ration ad-libitum throughout the test. At ten days of age, these are allocated to proper batteries according to sex. The compound 3 (p-methoxyphenyl)-4-n-propyl-7-hydroxycoumarin at 1 mg., 3 mg., 6 mg, 9 mg, and 12 mg. in paste implant form is injected subcutaneously in the dorsocervical region of the birds. This procedure is repeated at ten-day intervals for a period of thirty days. Each bird in the control batteries receives cc. placebo paste implant material on the same dates as the test birds. All birds are individually weighed and feed consumption measured at -day intervals in addition to each bird being individually wing-banded on the first injection date. At the conclusion of the test, necropsies are performed where indicated and final weights and feed consumption measured.

The weights and feed conversion at 10 days, days, and days (final) following the first implant for five such replicates are summarized in Tables I, II, and III. A response in weight gain and feed conversion, particularly with the female chicks, shows in the twenty and thirty day results. The ration fed the chicks was of the following composition:

Ground yellow corn 1000 Soybean meal, 44% 700 Fish meal, 60% 100 Alfalfa meal 50 Animal fat 80 Dicalcium phosphate Limestone 15 Iodized salt 10 Trace mineral mix-CCC 454 Choline supplement, 25% 2000 DL methionine 908 Proferm 24 227 Manganese sulfate 167 Vitamin A (30,000 IU/gm.) 200 Vitamin D (200,000 IU/gm.) 12 Santoquin 113 BY-24 120 Niacin, 98% Calcium pantothenate 36 Vitamin K (menadione), 32% 4 Vitamin E (myvamix) 113 Zinc oxide Zoamix 454 TABLE I [Average weights and feed conversion, ten-dayp0st injection] Control 1 mg. 3 mg. 6 mg. 9 mg. 12 mg.

Male-weights Rep. 1 382 332 385 396 392 398 2 383 382 396 373 394 390 3 380 402 386 389 379 383 4 396 358 379 386 408 385 5 392 389 386 386 393 368 Male-feed conversion Rep. 1. 62 1. 66 1. 56 1. 57 1. 39 1. 53 Rep. 1. 1. 53 1. 53 1. 50 1. 59 1. 51 Rep. 1. 54 1. 52 1. 1. 62 1. 53 1. 50 Rep. 1. 52 1. 54 1.53 1.53 1. 52 1. 52 Rep. 1. 48 1. 52 1. 50 1. 53 1. 45 1. 48

Female-weights I 1 361 346 355 336 348 310 2 308 313 352 340 350 353 3 302 330 313 313 319 333 4 336 314 311 330 325 330 Rep 5 308 300 318 3 309 329 Average. 323 321 330 326 330 331 Female-teed conversion Rep. 1. 51 1. 62 1. 57 1. 58 1. 57 1. 68 Rep. 1. 63 1. 62 1. 63 1.66 1. 56 1. 63 Rep. 1. 70 1. 60 1. 63 1. 62 1. 64 1. 70 Rep. 1. 54 1. 64 1. 72 1. 61 1. 62 1. 58 Rep. 1. 72 1. 76 1. 54 1. 66 1. 1. 60

Average..- 1. 62 1. 65 1. 62 1 63 1. 61 1. 64

TABLE II [Average weights and feed conversion, twenty-day-post injection] Control 1 mg. 3 mg. 6 mg. 9 mg. 12 mg.

Male-weights Rep. 1 695 587 708 708 697 726 Rep. 2 704 696 719 689 721 720 Rep. 3 713 726 701 719 706 703 Rep. 4 738 686 698 704 727 715 Rep. 5 712 711 700 703 730 680 Average. 712 681 705 705 716 709 Mnle1eed conversion Rep. 1 1. 84 1. 78 1. 1. 1. 59 1. 70 1. 65 1. 67 1. 66 1. 69 1. 74 1. 70 1. 66 1. 69 1. 72 1. 75 1.69 1. 69 1.67 1. 68 1. 71 1. 69 1. 72 1. 68 1. 66 1. 67 1. 66 1. 72 1. 64 1. 68

Female-weights Rep. 1 632 626 623 618 619 557 Rep. 2 519 550 633 618 619 591 Rep. 3 515 593 551 543 557 576 Rep. 4 595 575 549 573 557 560 Rep. 5 530 553 551 540 539 588 Average. 558 579 581 578 578 574 Femalefeed conversion Rep. 1 1. 71 1. 77 1. 77 1. 77 1. 80 1. 82 1. 80 1. 76 1. 76 1. 85 1. 77 1.83 1.88 1. 75 1. 79 1. 79 1. 81 1. 86 1. 76 1. 79 1. 86 1. 80 1. 79 1. 79 Rep. 5 1. 89 1. 80 1. 77 1. 82 1.84 1. 76

Average. 1. 83 1. 77 1. 79 1. 81 1. 80 1. 81

TABLE 111 [Average weights and feed conversion, tl1irty-doypost injection] Control 1 mg. 3 mg. 6 mg. 9 mg. 12 mg.

Male-weights Average- 1, 089 1,070 1,086 1,069 1,103 1, 079

TABLE IIICon tinued Control 1 mg. 9 mg. 6 mg. 9 mg. 12 mg.

I Male-feed conversion Female-feed conversion 1. 91 1. 94 1. 92 1. 92 1. 96 2.01 '1. 90 1. 90 l. 92 2. 1. 94 1. 93 1.93 l. 91 1. 92 1.98 1. 95 i 2. 00 1. 91 1. 92 1. 95 1. 93 1. 94 1. 91 1. 86 1. 93 1. 89 l. 92 1. 96 1. 95

Average 1. 90 1. 92 1. 92 1. 95 1. 95 1. 96

} EXAMPLE I II For the raising of broilers, i.e., starting with day-old to four-week-old chicks, a grower feed is prepared for feeding to the chicks for the first four weeks and a finisher feed is prepared for feeding the ifour-week-old chicks for the last five weeks until they reach market weight of two and a half to three pounds dressed. For each pound of weight gain, the-chicks eat about 1.5 to 2 pounds of feed. Thus, they eat about 1.5 pounds of feed during the first four weeks and about five pounds during the next five weeks. The grower and finisher feeds include, in addition to gm. (0.022 pounds) 3-(p-methoxyphenyl)-4-n-propyl-7-hydroxycoumarin, the following:

Grower Finisher (lbs.) (1bs.)

Ground yellow corn 1, 000 1, 200 Soybean meal (44% protein) 700 500 Fish meal (60% protein) 100 80 Alfalfa meal 50 50 Meat and bone scraps 5 0 Animal fat 80 80 Dicalcium phosphate v Iodized salt... .10 10 Limestone 15 Premix vitamins trace minerals and antibotics.... 10 10 EXAMPLE III ,Two groups of turkey poults are placed inseparate pensand fed the identical commercial feed of the 'follow- One part of the vitamin premix contains the following ingredients in such amount as to provide the following concentration in the final feed:

Percent Niacin 0.004 Calcium pentothenate 0.002 Riboflavin 0.0005 Folic acid 0.0001 Vitamin B 0.000002 Each group of these turkeys is maintained on this identical basal diet until reaching commercial sale weight. The premix has incorporated with its feed about 50 gms./ ton feed (about 0.005%) of the compound of Formula 1 based on the total weight of the feed to improve rate of weight gain.

EXAMPLE IV Three concentrate compositions are made by admixing respectively (1) 5.0 gm., (2) 25 gm., and (3) 50 gm. of the compound of Formula 1 with ground corn to make, in each case, a total concentrate mix of 250 grams.

A basal diet is prepared of the following ingredients, wherein the figures given are percent by Weight:

The vitamin supplement provides the following in milligrams per one hundred grams of diet:

Alpha-tocopherol 0.25 Niacin 2.00 D-calcium pantothenate 1.00 Riboflavin 0.25 Folic acid 0.05 Menadione 0.05 Vitamin B 0.0011 Choline chloride 50.00 Vitamin D supplement (3000 ICU/gram) 50.00

ing composition, whereimtheindicated amounts are percent by weight: H I

Y vPercent Com meal -..-.--.--..-:-.--.":---:---'-':-'r:- Soybean oil r'rieal dehull'ed V 32.00 Alfalfa meal, dehydrated'; 2.00 Fish meal 5.00 Whey (dried) 2.00 Brewers yeast -3.00 Livermeah H V i 2.00 7 Meat and bone meal 4.00 Prime beef tallow 5... 1, I 5.00 Calcite flour 2.00

Vitamin A supplement (5000 USP units/gram) 100.00

A coccidiostat can be added to the above as required.

,.Concentr.ates (1), (2) and (3) are admixed in suitable EXAMPLE V Choline chloride 0.02 Vitamin D supplement (3000 ICU/gram) 0.08 Vitamin A supplement (5000USP units/ gram) 0.40 Iodized salt j v H H 0.45 Manganese sulfate 0.05 Ca-methionine hydroxy'analog 0.05 Vitamin premix 1.00

Cross-bred Kentucky lambs are randomly allotted to treatment on the basis of sex, Weight and pretest performance. A control group and a test group, each containing 6 ewes and 8 wethers are obtained. The test group is fed 4.8 grams of'thecompound of Formula 1 per ton of feed.

Weight gain and feed efi'iciency data are recorded and analyzed for the six-week test period. The test results are:

* -6 weeks percent response as compared to control.

The test results show an 18.1% increase in feed efficiency (feed consumed/Weight gain) when the compound is used in the feed as compared to the control. The weight gain in percent of response compared to control was 23 0% ewes, 6.4% altered males and 12.6% both sexes.

LB. Finely ground corn cobs 715 Ground corn 330 Alfalfa meal 300 Dried molasses, 85% 120 Soybean meal, 44% 300 Dicalcium phosphate 14 TM salt Premix 214 1 Premix Lb. Ground corn 202 Limestone 4 Corn oil 2 Vitamin E (20,000 IU/lb.) 1 Baeiferm 40 1 111. Vitamin A (30.000 IU/gm.) 100 Vitamin D3 (200,000 IU/gm) 2 BY-24 (Riboflavin) 38 Calcium pantothenate 22.2 Niacin 38 Iroferm (Vitamin B12) 188.8

EXAMPLE VI The compound of Formula 1 is fed to cattle, swine and sheep in the manner described in Example V.

EXAMPLE VII Day-old Vantress Arbor Acres cross boiler chicks are obtained from a commercial hatchery, weighed in groups of thirty-three, allocated by sex to pens, and started on basal ration. At two Weeks of age, all birds are wingbanded and measurement of feed consumption started. At

four weeks of age, the birds are randomized according to weight and sex and the pens depopulated to twenty-five in number. Basal ration is fed to all pens except those wh ere treatment is administered orally and then the proper amount of the compound of Formula 1 on a per'ton basis is mixed in the feed as indicated. At the time the treatment is instituted, each bird in the approriate pen receives the proper amount of compound suspended in /2 cc. of paste implant material and those birds on medicated feed and controls are givena placebo paste implant of the same volume. Measurement of feed consumption is started at this time. At ten-day intervals the chicks are Weighed individually, according to number, and feed consumption is measured for the period. Two groups of birds are used for each amount of compound and control. At termination, all birds are individually weighed and weigh back of the feed is determined. The basal ration is:

Lb; Ground yellow corn 1000 Soybean meal, 44% A 700 Fish meal, 60% 100 Alfalfa meal 50 Animal fat V 80 Dicalcium phosphate Limestone l5 Iodized salt '10 Gm. Trace mineral mix-CSC 454 Choline supplement, 25% 2000 DL methionine 908 Proferm 24 227 Manganese sulfate 167 Vitamin A (30,000 IU/gm.) 200 Vitamin D (200,000 IU/gm.) 12 Santoquin 113 BY-24 120 Niacin, 98% 40 Calcium pantothe'riate 36 Vitamin K (Menadione), 32% 4 Vitamin E (Myvamix) "J; 113 Zinc oxide Zoamix 454 Weight gain and feed efficiency data is given in the tables below. The test results show that administration of the compound gives a response particularly with female chicks.

AVERAGE WEIGHT GAIN, 10- 20-30-DAY DATA I l 25 gm./ "gm./ Treatment Control 1 mg. 3 mg. 6 mg." 9 mg. 12 mg. T feed T feed 7 Malc10-day I I Rep. 1 1,137 1,119 1,140 1,133 1,151 1,114 1,129 1,121 Rep. 2 1,127 1,117 1,113 1,130 1,131 1,119 1,141

Average 1,132 1,118 1,131 1, 135 1, 141 1,117 1,135 1, 121

Fen1ale1O-day Rep. 1 914 936 922 928 937 921 938 937 Rep. 2 935 917 919 927 r 931 932 922 Average 925 926 921 928 934 927 930 937 Male20-day Rep. 1 1, 003 1,579 a 1,502 1,580 -1, 606 1, 500 1,586 1,576 Rep. 2 1,569 1,502 1,566 1,573 Y 1,557 1,550 1,610

Average 1, 580 1, 571 1, 570 1, 57 1, 581 '1, 555 1, 598 1, 570

, Female-20day Rep. 1 1,259 1, 273 1, 267 1, 266 1,278 ,1, 278 1, 293 1,301 Rep. 2 1,278 1, 260 1, 202 v 1, 269 1, 263v 1,267 1, 268 Average 1,268 1, 270 1, 265 H 1,268 1, 271 1, 272 1, 251 1, 301

Male-BO-day Rep. 1 2,110 2,101 2,181 2,125 2,122 2,057 2,104 2,105 Rep. 2 l, 131 2,103 2,098 2, 000 2,117 2,086 2,130

Average 2, 125 2, 2, 140 2, 111 2, 2, 072 2, 120 2, 105

AVERAGE WEIGHT GAIN, 30-DAY DATA Continued 1 5o Treatment Control 1 mg. 3 mg. 6 mg. 9 mg. 12 mg. T f e r ed T f ed V Female-30629 Rep- 1 1, 653 1, 648 1, 679 1, 649 1, 765 1, 649 1, 677 1, 706 Re 2 1,622 A 1,683 1,660 1,674 1,664 1,661 1,631

Average 1,638v "1 1,666 1,670 1,661 1,665 1,655 1,654 1,706

FEED CONVERSION, 10- 2O -DAY DATA I I 25 gm./ 50 gm./ Treatment Control 1 1 mg. 3 mg; I 6 mg. 9 mg. 12 mg. T teed T feed Male-10-day Rep. 1 1.71 1. 77 1.71 '1. 66 1.44 1.77 1.74 1.72 Re 2 1. 73 1. 74 1. 78 1. 70 1. 75 1. 74 9. 69

Average 1.72 1.76 1.75 1.68 1.60 1. 76 1.72 1.72

. Female-10-day Re 1.83 1.76 1.82 1.80 1.80 1.83 1.78 1.85 Re 1. 80 1. 86 1.89 1.82 1.79 1.77 1. 76

Average 1.82 1.81 1.86 1.81 1.80 1. 80 1. 77 1.85

Ma1e20-day Re 1 2. 01 2. 06 2. 09 1. 96 1. 82 2. 07 2. 63 2. 02 Re 2 2.02 7 2.04 2.06 2.04 2.17 2.06 2.01

Average 2. 02 i 2. 2. 08 2. 00 2. 00 2. 07 2. 20 2. 02

\71 Female-20-day Re 1 e. 2.11 2. 07 2. 07 2.11 2.12 2. 11 2. 07 2.10 Re 2 2.13 1 2.12 2. 16 2.13 2.12 2.11 2. 07

Average 2.12 2. 2.12 2.12 2.12 2.11 2.07 2.10

Male-Bowery Re 2.25 2.24 2.18 2.15 2.10 2.28 2.24 2.25 Rep. 2.20 2.21 2.27 2.28 2. 36 2.27 2.26

I Female-6041a Re 1 2. s4 2. 29 2.31 1 2. 83 2.24 2.38 2.31 2. 32 Rep. 2 2.39 2.31 2. 2. 36 L 2. 35 2. 38 2. 33

Average 2. 36; 2. 30, 2.36 2.35 2. 2.38 2.32 2.32

I i p EXAMPLES VIII Toxn 4 2 The compound 3 -(p-hydroxyphenyl)-4-n-propyl-7-hy- 2 OR droxycoumarin instead of the compound of 'Formula. 1 is cu employed in the same amounts and in the same manner set forth in Examples 11, III, IV, V and VI.

' HO 0 o EXAMPLES XDIE TO XVII The compound 3 (p benzyloxyphenyl)-4-n-propyl-7 hydroxycoumarin instead of the compound of Formula 1 is employed in the same amounts and in the same manner set forth in Examples II, HI, IV, V and V1.

The coumarin compounds employed in the present invention are known and can be prepared, for instance, in accordance with a procedure described in Bulletin of the Societe Chimique of France, 1946, pp. 271-276 by Mentzer et 6.1. (vol. 13). For instance, p-methoxyphenylaceto nitrile can be used to prepare the compound of Formula 1; p-hydroxyphenylacetonitrile can be used to prepare 3 (p hydroxyphenyl)-4-n-propy1-7-hydroxycoumarin; and p-benzyloxyphenylacetonitrile can be used to prepare 3-(p-benzyloxyphenyl)-4-n-propyl-7-hydroxycoumarin.

The foregoing detailed description has been given for clearness of understanding only and no unnecessary 1i1nitations are to be understood therefrom.

The invention claimed is:

1. A poultry feed composition comprising a poultry fed and suflicient amounts of one of the following compounds to provide improved weight gain in the animal consuming the feed:

wherein R is hydrogen, lower alkyl or benzyl.

where R is hydrogen, lower alkyl or benzyl.

8. The composition of claim 7 wherein the amount is from about 1 to 150 grams compound per ton feed.

9. A method of improving the rate of growth of swine comprising feeding to the swine one of the compositions of claim 7 in an amount effective to improve the rate of Weight gain of the swine.

10. A method of increasing the rate of growth of meat-producing animals comprising administering orally or parenterally to the animal one of the compounds 3-(plower alkoxyphenyl) 4 n propyl-7-hydroxycoumarin, 3 (p hydroxyphenyl) 4 n propyl 7 hydroxycoumarin or 3 (p benzyloxyphenyl)-4-n-propyl-7-hydroxycoumarin in an amount and for a time effective to increase the rate of growth, said amount being from about 0.0001% to about 0.02% by weight based upon the total weight of the animals feed.

11. A poultry feed composition comprising a poultry feed and sufficient amounts of the following compound to provide improved weight gain in the animal consum- 7 ing the feed: 1

E CH2 12. The composition of claim 11 wherein the amount is from about 1 to 150 grams of compound per ton feed. 13. A method of improving the rate of growth of poultry comprising feeding to the poultry the composi- 12 tion of claim 11 in an amount effective to improve the rate of weight gain of the poultry.. 14. A ruminant feed composition comprising a ruminant feed and sufficient amounts of the following compound to provide improved weight gain in the animal consumingthefeed: a

9H oca 15. The composition of claim 14 wherein the amount is from about 1 to grams compound per ton feed.

16. A method of improving the rate of growth of ruminants comprising feeding to the ruminants the compositon of claim 14 in an amount effective torimprove the rate of Weight gain of the ruminants.

17. A swine fed composition comprising a swine feed and sufficient amounts of the following compound to provide improved weight gain in the animal consuming the feed:

18. The composition of claim '17 wherein the amount is from about 1 to 150 grams compound per ton feed. 19. A method of improving the rate of growth of swine comprising feeding to the swine the composition of claim 17 in an amount effective to improve the rate of weight gain of the swine.

20. A method of increasing the rate of growth of meatproducing animals comprising administering orally or parenterally to the animal the compound '3'-(p-metho'xyphenyl) 4 n propyl 7 hydroxycoumarin in an amount and for a time effective to increase the rate of growth, said amount being from about 0.0001% to about 0.02% by weight based upon the total weight of the animals feed.

References Cited Pasault, Chem. Abst. vol. 42 (.1948), p. 4409 (441 021).

SAM ROSEN, Primary Examiner I 

